CN115429759B - Preparation method and application of liposome taking rhizoma paridis saponin active extract as membrane material - Google Patents
Preparation method and application of liposome taking rhizoma paridis saponin active extract as membrane material Download PDFInfo
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- CN115429759B CN115429759B CN202211016196.4A CN202211016196A CN115429759B CN 115429759 B CN115429759 B CN 115429759B CN 202211016196 A CN202211016196 A CN 202211016196A CN 115429759 B CN115429759 B CN 115429759B
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1277—Processes for preparing; Proliposomes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention discloses a preparation method and application of liposome taking rhizoma paridis saponin active extract as a membrane material. The method takes the paris polyphylla saponin, cholesterol and phospholipid as raw materials, utilizes the characteristic that the paris polyphylla saponin has a steroid structure, takes the paris polyphylla saponin active extract as a liposome membrane material to prepare the liposome, and has the characteristics of low hemolysis, high safety, good film forming property and excellent stability. The novel liposome prepared by the invention and taking the rhizoma paridis saponin active extract as a membrane material can be efficiently enriched in tumor cells and inhibit proliferation of the tumor cells, and the antitumor effect of the liposome is improved by utilizing the glycosyl structure and antitumor pharmacological action of the rhizoma paridis saponin.
Description
Technical Field
The invention relates to the field of biological pharmacy, in particular to a preparation method of liposome taking rhizoma paridis saponin active extract as a membrane material.
Background
In the existing anti-tumor treatment method, single-target drug treatment is difficult to meet treatment requirements, and clinical test results show that the multi-target inhibitor is superior to the single-target inhibitor in treatment, so that the toxic and side effects of traditional treatment can be reduced, and drug resistance possibly caused by single-target treatment can be eliminated.
The Chinese medicine paris polyphylla has the pharmacological actions of clearing heat and detoxicating, detumescence and relieving pain, cooling liver and arresting convulsion, and the paris polyphylla is often formed into a prescription for treating cancers, so that the drug resistance and the life quality of patients can be improved. The pain-relieving anticancer pill mainly composed of rhizoma paridis has better pain-relieving effect for advanced cancer.
The paris polyphylla saponin is the main active ingredient of paris polyphylla, and accounts for more than 80% of the total compounds, and the paris polyphylla saponin extract contains various active monomer steroid saponins, including paris polyphylla saponin I, paris polyphylla saponin II, paris polyphylla saponin VI, paris polyphylla saponin VII and the like, and can resist tumors through various mechanisms such as pro-apoptosis, anti-inflammatory, anti-angiogenesis, tumor cell signal transduction inhibition and the like, and the antitumor effect is greatly superior to that of a single active monomer.
However, paris polyphylla saponin has strong intravenous injection and hemolysis, poor oral absorption, poor drug-forming property, and severely limited clinical application. The paris polyphylla saponin has steroid structure, has the function of regulating phospholipid fluidity similar to cholesterol, and can be used as a membrane material for preparing liposome. The paris polyphylla saponin also contains glycosyl structure, can be taken up by tumor cells through GLUT1, and after the liposome is taken up by tumor cells, the released paris polyphylla saponin can inhibit proliferation of tumor cells, can be used for treating tumors in cooperation with the loaded medicine, and is a novel liposome for treating tumors with high efficiency.
Disclosure of Invention
The invention aims to provide a preparation method and application of liposome taking rhizoma paridis saponin active extract as membrane material, which are used for anti-tumor treatment. The paris polyphylla saponin has steroid structure, and the paris polyphylla saponin is used as liposome membrane material to prepare liposome, so that the hemolysis of paris polyphylla saponin can be reduced, and the drug property and safety of paris polyphylla saponin are improved. Meanwhile, the paris polyphylla saponin has glycosyl structure and anti-tumor pharmacological action, can be efficiently enriched in tumor cells through GLUT1, and the released various paris polyphylla saponin active monomer molecules can inhibit proliferation of the tumor cells through various mechanisms.
The technical scheme of the invention is as follows: a method for preparing liposome by using rhizoma paridis saponin active extract as membrane material comprises separating rhizoma paridis saponin active extract by ethanol extraction-column chromatography method, and preparing liposome by membrane hydration-ultrasonic method by using rhizoma paridis saponin active extract as membrane material with steroid characteristic. Accurately weighing rhizoma paridis saponin active extract, cholesterol and phospholipid (saponin: cholesterol: phospholipid=2:1:10, w/w/w), and dissolving in appropriate amount of anhydrous methanol/dichloromethane (1:1, v/v). The organic solvent was removed by rotary evaporation under reduced pressure in a 45℃water bath to form a thin and uniform lipid film. After the lipid membrane is dried, injecting a proper amount of nitrogen to protect the lipid membrane, adding pH 7.4PBS, hydrating in 55 ℃ water bath, and performing ultrasonic treatment for 3min (ultrasonic power 300W) to obtain the liposome taking the rhizoma paridis saponin active extract as a membrane material.
The invention utilizes the glycosyl structure of the paris polyphylla saponin to promote the paris polyphylla saponin to be efficiently enriched in tumor cells through GLUT1 transport on the surfaces of the tumor cells, and the released plurality of paris polyphylla saponin active monomers can inhibit the proliferation of the tumor cells through a plurality of mechanisms and can cooperate with the carried medicines to resist tumors.
The innovation of the invention is as follows: (1) by utilizing the characteristic that the paris polyphylla saponin has a steroid structure, the active extract of paris polyphylla saponin is used as a membrane material to prepare the liposome which uses the active extract of paris polyphylla saponin as the membrane material, so that the hemolysis of the active extract of paris polyphylla saponin is obviously reduced. (2) The prepared liposome can be efficiently enriched in tumor cells through GLUT1 mediation on the surfaces of the tumor cells, inhibit proliferation of the tumor cells, and improve the anti-tumor effect of a drug delivery system.
Drawings
FIG. 1 is an extraction flow of rhizoma paridis saponin active extract.
FIG. 2 is a component measurement of the active extract of paris polyphylla saponin.
FIG. 3 shows the main active monomers contained in the active extract of paris polyphylla saponin.
FIG. 4 is a graph showing the particle size distribution and transmission electron microscopy of liposomes containing the active extract of paris polyphylla saponin as a membrane material.
FIG. 5 shows the storage stability of liposomes containing the active extract of paris polyphylla saponin as a membrane material.
FIG. 6 shows the hemolysis of liposomes containing the active extract of paris polyphylla saponin as a membrane material.
FIG. 7 shows GL261/TR tumor cytotoxicity of liposomes containing rhizoma paridis saponin active extract as membrane material.
Detailed Description
1 study method
1.1 extraction and identification of Paris polyphylla saponin active extract
(1) Separating rhizoma paridis saponin active extract (figure 1) by ethanol extraction-column chromatography method:
weighing 500g of paris polyphylla rhizome, slicing, pulverizing into powder, reflux-extracting at 80 ℃ for 1.5h each time, and performing ultrasonic assistance. First, 5000ml of 95% ethanol (10 times the ratio of the liquid medicine) was added, and second, 4000ml of 70% ethanol (8 times the ratio of the liquid medicine) was added. Eight layers of gauze are used for filtering, and the two extracting solutions are combined. Taking 200ml of the extract, drying under reduced pressure, centrifuging at 3500r/min for 30min, precipitating, evaporating in water bath at 60deg.C, evaporating supernatant under reduced pressure, and concentrating until no alcohol smell. Extracting the extractive solution with dichloromethane, water and saturated n-butanol sequentially four times to obtain rhizoma paridis saponin crude extract.
600g of silica gel is taken, the column is packed by a chloroform wet method, and the column is stood overnight. Dissolving rhizoma paridis saponin crude extract in methanol, adding appropriate amount of silica gel, stirring, volatilizing solvent, loading on column, gradient eluting with dichloromethane-methanol-water (50:1:0.1; 10:1:0.1;5:1:0.1;60:35:10;5:5:2, v/v/v), performing TLC identification on each 400ml, recovering solvent under reduced pressure, and recrystallizing with anhydrous ethanol to obtain purified rhizoma paridis saponin active extract.
TLC identification: taking 10 μl of the sample solution and the reference substance solution, respectively spotting on the same silica gel thin layer plate, spreading with lower layer solution of chloroform-methanol-water (15:5:1) as spreading agent, taking out, air drying, spraying 10% sulfuric acid ethanol solution, heating at 105deg.C until the color of spots is clear, and respectively placing under sunlight and ultraviolet lamp (365 nm) for inspection.
(2) Identification of active ingredients in paris polyphylla saponin extract:
UPLC chromatographic conditions: a 100mm c18 column; mobile phase acetonitrile (a) and water (B); gradient elution procedure: 0-20min, 30-60% of A,20-25min, 60-30% of A; detection wavelength: 203nm; flow rate: 0.2ml/min; sample injection amount: 5 μl; column temperature: 30 ℃.
Preparing a reference substance solution: taking appropriate amounts of rhizoma paridis saponin I reference substance, rhizoma paridis saponin II reference substance, rhizoma paridis saponin VI reference substance and rhizoma paridis saponin VII reference substance, precisely weighing, adding methanol to obtain mixed solutions each containing 0.4mg per 1ml, and sampling under the above UPLC chromatographic conditions.
Preparation of test solution: weighing the extracted rhizoma paridis saponin active site, dissolving in methanol solution, and sampling under the UPLC chromatographic conditions.
1.2 preparation and characterization of Liposome Using Paris polyphylla saponin active extract as Membrane Material
(1) Preparing liposome with rhizoma paridis saponin active extract as membrane material by using thin film hydration-ultrasonic method: the liposome is prepared by using the characteristic that the paris polyphylla saponin has a steroid structure and the paris polyphylla saponin active extract as a membrane material. Accurately weighing rhizoma paridis saponin active extract, cholesterol and phospholipid (saponin: cholesterol: phospholipid=2:1:10, w/w/w), and dissolving in appropriate amount of anhydrous methanol/dichloromethane (1:1, v/v). The organic solvent was removed by rotary evaporation under reduced pressure in a 45℃water bath to form a thin and uniform lipid film. After the lipid membrane is dried, injecting a proper amount of nitrogen to protect the lipid membrane, adding pH 7.4PBS, hydrating in 55 ℃ water bath, and performing ultrasonic treatment for 3min (ultrasonic power 300W) to obtain the liposome taking the rhizoma paridis saponin active extract as a membrane material.
(2) Characterization of liposomes: 0.2ml of the liposome solution was diluted with 0.8ml of distilled water, and then the particle size, polydispersity index (PDI) and zeta potential were measured by using a laser particle size analyzer and zeta potential. Meanwhile, a proper amount of liposome solution is dripped in the middle of a copper mesh of the carbon support film, and the carbon support film is naturally dried in air. After 1% phosphotungstic acid is dyed for 1min, a proper amount of grade I water is added dropwise and the mixture is sucked dry by filter paper, and the excess phosphotungstic acid is washed off. Appearance of liposomes by transmission electron microscopy
(3) Determination of the content of Paris polyphylla saponin active extract in liposomes: the column was a Dikma ODS C18 column (100 mm. Times.2.1 mm,3 μm), the detection wavelength was 210nm, the mobile phase acetonitrile (A) and water (B), gradient elution procedure: 0-20min, 30-60% A,20-25min, 60-30% A, flow rate: sample injection amount of 0.2 ml/min: 5 μl, column temperature: 30 ℃. Taking 1ml of liposome solution, adding 1ml of methanol, carrying out ultrasonic treatment for 2min, filtering with a 0.22 mu m microporous filter membrane, carrying out sample injection according to the chromatographic conditions, recording peak areas, and calculating the concentration of the rhizoma paridis saponin active extract according to a working curve.
(4) Stability investigation of liposome taking rhizoma paridis saponin active extract as membrane material: a certain amount of liposome solution using rhizoma paridis saponin active extract as a membrane material is measured periodically, and the storage stability of the liposome using rhizoma paridis saponin active extract as a membrane material is measured by a laser particle size analyzer.
1.3 haemolysis of liposomes
Blood was collected from the abdominal aorta of anesthetized SD rats using a vacuum blood collection tube for 5mL, centrifuged at 3000r/min for 5min, and the supernatant was aspirated and washed with physiological saline, and repeated 3 times. 1mL of the lower layer red blood cells were precisely measured, and a physiological saline suspension of 2% red blood cells was prepared. Liposome solutions of different concentrations, 1mL of which the active extract of rhizoma paridis saponin is taken as a membrane material, are prepared by using physiological saline, and equal volumes of physiological saline and purified water are taken as a negative control and a positive control. 1mL of a physiological saline suspension of 2% erythrocytes was added to the above solutions, mixed gently, and incubated in a constant temperature incubator at 37℃for 3 hours. After 1h and 3h, respectively, centrifugation is carried out for 5min at 3000r/min, and photographing is carried out under the white back. 200. Mu.l of the supernatant was precisely measured, absorbance of each group at 450nm was measured in an ultraviolet spectrophotometer, and the hemolysis ratio (%) = (sample absorbance-negative control absorbance)/(positive control absorbance-negative control absorbance) ×100% was calculated.
1.4 Effect of liposomes on proliferation of tumor cells
Inoculating GL261/TR cells in a logarithmic growth phase into a 96-well plate, after 24 hours, discarding an upper-layer culture solution, adding a liposome solution which is diluted by a serum-free DMEM culture solution and takes a rhizoma paridis saponin active extract as a membrane material (taking a free rhizoma paridis saponin active extract as a reference), adding 200 mu l of each well, incubating for 48 hours, adding MTT reagent with the concentration of 5mg/ml, adding 20 mu l of each well, incubating for 4 hours, discarding the upper-layer culture solution, adding 200 mu l of DMSO (DMSO) each well, shaking for 10 minutes, detecting the absorbance value at 560nm by adopting an enzyme-linked immunosorbent assay (ELISA) to calculate the cell survival rate of each group, and investigating the influence of the liposome which takes the rhizoma paridis saponin active extract as the membrane material on the proliferation of GL261/TR cells.
2 experimental results
2.1 identification of Paris polyphylla saponin active extract
And (3) identifying the extracted rhizoma paridis saponin active extract by adopting UPLC, and taking a proper amount of rhizoma paridis saponin I reference substance, rhizoma paridis saponin II reference substance, rhizoma paridis saponin VI reference substance and rhizoma paridis saponin VII reference substance for sample injection, wherein the result is shown in figure 2, and the extracted rhizoma paridis saponin active extract mainly contains active rhizoma paridis saponin monomers such as rhizoma paridis saponin I, rhizoma paridis saponin II, rhizoma paridis saponin VII and the like, and the structure of the main active monomers is shown in figure 3.
2.2 characterization of liposomes with Paris polyphylla saponin active extract as Membrane Material
The particle size and potential of liposome using rhizoma paridis saponin active extract as membrane material were measured by nanometer particle size analyzer, and the result is shown in fig. 4 (a), the particle size of liposome is 101nm, and the liposome is spherical under electron microscope, round in appearance and uniform in size, as shown in fig. 4 (B). The liposome has potential of-4 mV and contains rhizoma paridis saponin active extract 16.9%. The results of the stability test of the liposome using the active extract of paris polyphylla saponin as a membrane material are shown in fig. 5, and the particle size and PDI of the liposome are not obviously increased during the storage period of 10 days, which suggests that the stability of the liposome is good.
2.3 haemolysis of liposomes
As shown in FIG. 6 (A), the free rhizoma paridis saponin active extract had a significant hemolysis at 1. Mu.g/ml when tested for hemolysis for 1h, whereas liposomes did not have a significant hemolysis at 100. Mu.g/ml. As shown in FIG. 6 (B), the free rhizoma paridis saponin active extract has remarkable hemolysis, EC 50 Only 1.84 mug/ml, while the liposome can significantly reduce the hemolysis of the active extract of paris polyphylla saponin, EC 50 The liposome prepared by taking the active extract of the paris polyphylla saponin as a membrane material is improved to 144.20 mug/ml, so that the hemolysis of the free paris polyphylla saponin can be greatly reduced, and the drug property of the liposome is improved.
2.4 Effect of liposomes on proliferation of tumor cells
MTT results are shown in FIG. 7 (A), the IC of 24h of the free paris polyphylla saponin active extract on GL261 cells 50 For 9.077. Mu.g/ml, as shown in FIG. 7 (B), liposome 24h has an IC for GL261 cells 50 At 0.13. Mu.g/ml, as shown in FIG. 7 (C), liposome 48h IC against GL261 cells 50 0.08 mug/ml, which suggests that after liposome preparation, the aggregation of the active extract of the paris polyphylla saponin in tumor cells can be increased, the proliferation inhibition effect on the tumor cells is obviously increased, and the inhibition effect is time and dose dependent. Conclusion 3:
the active extract of the paris polyphylla saponin is separated by adopting an ethanol extraction-column chromatography method, and the liposome taking the paris polyphylla saponin as a membrane material is prepared by adopting a membrane hydration-ultrasonic method, so that the liposome has good stability, can obviously reduce the hemolytic property of intravenous injection, can be efficiently enriched in tumor cells and obviously inhibit the proliferation of the tumor cells, and has a certain application prospect.
Claims (2)
1. A preparation method of liposome taking rhizoma paridis saponin active extract as membrane material is characterized in that ethanol extraction-column chromatography method is adopted to separate and obtain rhizoma paridis saponin active extract, the characteristics of steroid are utilized, the rhizoma paridis saponin active extract is taken as membrane material, and membrane hydration-ultrasonic method is adopted to prepare liposome; accurately weighing rhizoma paridis saponin active extract, cholesterol and phospholipid, and dissolving in appropriate amount of anhydrous methanol/dichloromethane; removing the organic solvent by reduced pressure rotary evaporation in a water bath at 45 ℃ to form a thin and uniform lipid film; after the lipid membrane is dried, injecting a proper amount of nitrogen to protect the lipid membrane, adding PBS with pH of 7.4, hydrating in a 55 ℃ water bath, and performing ultrasonic treatment for 3min under ultrasonic power of 300W to obtain the liposome taking the rhizoma paridis saponin active extract as a membrane material; wherein the saponins are calculated by weight: cholesterol: phospholipid=2:1:10, absolute methanol by volume: dichloromethane=1:1.
2. The use of the liposome prepared by the preparation method of the liposome taking the rhizoma paridis saponin active extract as a membrane material in preparing medicines for treating tumor diseases according to claim 1.
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